Which reagents would convert $c i s -$ $3$ $- h e x e n e$ to $m e s o -$ $3, 4$ $- h e x e n e d i o l ?$

O s O_{4}, (C H_{3})_{3} C C O O H, (C H_{3})_{3} C O H, N a O H

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O_{3}

followed by

Z n / H_{2} O

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B_{2} H_{6} /

diglyme followed by

H_{2} O_{2} / N a O H

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C H_{3} C O_{3} H

followed by

N a O H / H_{2} O

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Solution

The correct option is A $O s O_{4}, (C H_{3})_{3} C C O O H, (C H_{3})_{3} C O H, N a O H$
The osmium tetroxide adds to the double bond of an alkene in a concerted mechanism forming an osmate ester. The osmate ester can be hydrolized to produce a cis- glycol and regenerate the osmium tetroxide.
Ozonolysis $O_{3} + Z n / H_{2} O$ splits the alkene at double bond and forms two aldehydes.
Hydroboration $B_{2} H_{6} + H_{2} O_{2} / N a O H$ forms alcohol.
Peracid forms epoxide with alkene. Epoxide on reaction with $N a O H / H_{2} O$ produce trans vicinal diol.

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Similar questions

Q. Which of the reagents shown below would accomplish the following transformations?

(A)	(B)
1) $H_{3} O^{+}$	$B H_{3} T H F; H_{2} O_{2} / N a O H$
2) NaOH	$B H_{3} T H F; H_{2} O_{2} / N a O H$
3) HBr in ether	$H g (O A c)_{2} / H_{2} O; N a B H_{4}$
4) $N a N H_{2}$	$H g (O A c)_{2} / H_{2} O_{2}; N a B H_{4}$

Q. Cis-3-hexene

(a) - \to

meso 3,4-hexanediol
trans-3-hexene

(b) - \to

meso 3,4-hexanediol.
Choose pair of reagent (a, b) for above conversions.

Propene $C H_{3} - C H = C H_{2}$ can be converted into 1-propanol by oxidation. Which set of reagents among the following is ideal to affect the conversion ?

Q. What reagent and/or reaction sequence below would convert trans-

3

-hexene to meso-

3, 4

-hexanediol?

Q. What would be the product formed upon treatment of (Z)-

3

-methyl-

3

-hexene with

B_{2} H_{6}

followed by treatment with

H_{2} O_{2},^{-} O H

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Which reagents would convert cis−3−hexene to meso−3,4−hexenediol?

Which reagents would convert $c i s -$ $3$ $- h e x e n e$ to $m e s o -$ $3, 4$ $- h e x e n e d i o l ?$